Shady Side Rentals

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125 Houses

180-degree water views at unique round house

Shady Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$367

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$429

Great rentals within 20 miles that match your search

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$715

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

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Price per night from

$486

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

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Price per night from

$452

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$475

Love Point Waterfront

Kent Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

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Price per night from

$458

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,944

One Beautiful home come relax

Cheltenham house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$201

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$1,944

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$801

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,144

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$399

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,287

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$401

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,287

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,859

Brazilian Artsy Townhome- The wooded getaway

Cape Saint Claire house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$343

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$441

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$457

Waterfront Getaway - View of bay from your bed

Romancoke studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$228

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$629

Bahia Breeze - Beachfront Cottage

Chesapeake Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$226

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$342

London Towne Bungalow w/Loft

Edgewater bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$298

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$571

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,544

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$223

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$315

South River Hangout

Edgewater tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 16

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Price per night from

$343

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$681

Neptunes by the Water

Cape Saint Claire house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$206

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$429

Cozy Downtown Annapolis Apartment

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$247

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$441

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$189

Annapolis Woodland Retreat

Cape Saint Claire house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$343

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,887

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rentals in Shady Side

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